769-60-8

Basic information

• Product Name: 2-methyl-1-phenyl-prop-2-en-1-one
• Synonyms: 2-methyl-1-phenyl-prop-2-en-1-one;(1-Methylvinyl)phenyl ketone;Methacrylophenone;Methacryloylbenzene;Phenyl(1-methylethenyl) ketone;Phenylisopropenyl ketone;α-Methylacrylophenone
• CAS NO: 769-60-8
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.19
• Mol File: 769-60-8.mol
• Article Data: 90

Chemical Properties

• Boiling Point: 221.6°C at 760 mmHg
• Flash Point: 83.8°C
• Appearance: /
• Density: 0.981g/cm³
• Vapor Pressure: 0.106mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 2-methyl-1-phenyl-prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-1-phenyl-prop-2-en-1-one(769-60-8)
• EPA Substance Registry System: 2-methyl-1-phenyl-prop-2-en-1-one(769-60-8)

Safety Data

• Hazardous Substances Data: 769-60-8(Hazardous Substances Data)

Usage

Description

2-methyl-1-phenyl-prop-2-en-1-one, also known as 2-methyl-1-phenyl-1-propen-1-one or cinnamaldehyde methyl ether, is an organic compound that features a phenyl group attached to a methyl-substituted prop-2-en-1-one moiety. It is characterized by its aromatic properties and reactivity, making it a versatile intermediate in organic synthesis.

Uses

Used in Pharmaceutical Industry:
2-methyl-1-phenyl-prop-2-en-1-one is used as a chemical reagent for the synthesis of various pharmaceutical agents, such as isoquinolines or tetrahydroquinolines. Its unique structure allows it to participate in a range of chemical reactions that facilitate the production of these bioactive compounds, which are important in the development of medications for treating various diseases and conditions.

Synthesis Reference(s)

Synthetic Communications, 17, p. 1823, 1987 DOI: 10.1080/00397918708077327Tetrahedron Letters, 21, p. 4283, 1980 DOI: 10.1016/S0040-4039(00)92884-3

InChI:InChI=1/C10H10O/c1-8(2)10(11)9-6-4-3-5-7-9/h3-7H,1H2,2H3

Upstream product

• 50-00-0 formaldehyd 
• 93-55-0 1-phenyl-propan-1-one 
• 67-64-1 acetone 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 7473-98-5 2-hydroxy-2-methylpropiophenone 
• 104722-72-7 C₂₄H₂₅NOSe₂ 
• 104722-78-3 C₂₀H₂₂O₃Se 
• 17231-17-3 2-methyl-1-oxo-1-phenylpropan-2-yl methanesulfonate 
• 64-19-7 acetic acid 
• 69358-42-5 1-phenyl-2-(phenylsulfinyl)-1-propanone 
• 81360-92-1 2-benzoyl-2-propaneseleninic acid 
• 119044-26-7 3-ethylthio-2-methyl-3-phenyl-prop-2-ene-1-ol 
• 116981-02-3 3-iodo-1-trimethylsiloxypropene 

Downstream Products

• 5278-43-3 3-methyl-2-phenyl-quinoline 
• 15775-35-6 2-methyl-1-phenylhept-6-en-1-one 
• 125540-58-1 2-methyl-1-phenylhept-6-en-1-one 
• 4383-08-8 (S)-(+)-2-methyl-1-phenyl-2-propen-1-ol 
• 336883-15-9 C₁₂H₁₄O₂ 
• 103729-80-2 2-methyl-1-phenylprop-2-en-1-ol 
• 1255940-73-8 [InCl(C₆H₅COCH(CH₃)CH₂)2] 
• 123716-68-7 1-(4-methyl-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone 

Relevant articles and documents

A Novel Synthesis of β-Trichlorostannyl Ketones from Siloxycyclopropanes and Their Facile Dehydrostannation Affording 2-Methylene Ketones

Site-selective ring cleavage of siloxycyclopropanes 2 with stannic chloride (SnCl4) leads to good yields of β-trichlorostannyl ketones 3.Subsequent treatment of 3 with dimethyl sulfoxide (Me2SO) in chloroform at 60 deg C results in the facile dehydrostannation to give good yields of 2-methylene ketones 4.

Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents

An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.

Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol

One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.